My wife got me a second-generation Shuffle for Christmas, and I love it, but I noticed something odd: when I load a combination of music and podcasts onto it, the podcasts refuse to play in the order that they're listed in the iTunes Shuffle window. (No, I did not have it set to shuffle.) Rather, they play in chronological order, come hell or high water.

A sampling of websites suggested that many people consider this behavior to be normal and unchangeable. It seems that it is neither. According to this item from the Apple discussions board, the solution is to throw out (or, better, archive!) your iTunes Library file from ~/Music/iTunes/, then restart iTunes and rebuild the library from scratch. Specifically, use File / Add to Library... and select your iTunes Music folder, then sit for a few minutes while it chugs away. Best to be connected to the Internet so that iTunes can re-import album art.

Note that this will wipe out most or all of your playlists. But I tried it, and it solved my problem -- my podcasts now play in the order that I have them loaded.

Listen to podcasts in order on an iPod Shuffle
Authored by: creed on Jan 16, '07 04:13:02PM

Or you could get them into an appropriate order by using the column headers in iTunes when viewing the shuffle's contents, then right-click on the shuffle icon in the left column and select 'Copy To Play Order'.

This will set the shuffle to play its contents back (assuming you don't have the shuffle mode on) in that order.

Listen to podcasts in order on an iPod Shuffle
Authored by: tinker on Jan 18, '07 11:39:02AM

To be clear: There are apparently a fair number of Macs out there that act in a very subtly defective manner when it comes to podcasts and Shuffles. We're not talking about the right way to do it when your Mac works properly (in which case both of the above are fine solutions); we're talking about how to fix your Mac when it doesn't.